Trifunctional Fluorogenic Probes for Fluorescence Imaging and Isolation of Glycosidases in Cells

Ji Young Hyun; Seong Hyun Park; Cheol Wan Park; Han Byeol Kim; Jin Won Cho; Injae Shin

doi:10.1021/acs.orglett.9b01147

Trifunctional Fluorogenic Probes for Fluorescence Imaging and Isolation of Glycosidases in Cells

Ji Young Hyun, Seong Hyun Park, Cheol Wan Park, Han Byeol Kim, Jin Won Cho, Injae Shin

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

For both fluorescence imaging and isolation of glycosidases in cells, we prepared novel activity-based, trifunctional fluorogenic probes that consist of (1) a sugar moiety as a glycosidase substrate, (2) a fluoromethylated coumarin for fluorescent labeling, and (3) an alkyne tag for click reaction to enable isolation of the labeled enzyme. One probe, β-GlcNAc-CM-F, was employed to fluorescently detect endogenous O-GlcNAcase in cells and to isolate the labeled enzyme by affinity chromatography.

Original language	English
Pages (from-to)	4439-4442
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.9b01147
Publication status	Published - 2019 Jun 21

Bibliographical note

Funding Information:
This study was supported financially by the National Creative Research Initiative program (Grant No. 2010-0018272 to I.S.) and the National Research Foundation (Grant No. NRF-2016R1A5A1010764 to J.W.C).

Publisher Copyright:
© 2019 American Chemical Society.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b01147

Cite this

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title = "Trifunctional Fluorogenic Probes for Fluorescence Imaging and Isolation of Glycosidases in Cells",

abstract = "For both fluorescence imaging and isolation of glycosidases in cells, we prepared novel activity-based, trifunctional fluorogenic probes that consist of (1) a sugar moiety as a glycosidase substrate, (2) a fluoromethylated coumarin for fluorescent labeling, and (3) an alkyne tag for click reaction to enable isolation of the labeled enzyme. One probe, β-GlcNAc-CM-F, was employed to fluorescently detect endogenous O-GlcNAcase in cells and to isolate the labeled enzyme by affinity chromatography.",

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AU - Hyun, Ji Young

AU - Park, Seong Hyun

AU - Park, Cheol Wan

AU - Kim, Han Byeol

AU - Cho, Jin Won

AU - Shin, Injae

N1 - Funding Information: This study was supported financially by the National Creative Research Initiative program (Grant No. 2010-0018272 to I.S.) and the National Research Foundation (Grant No. NRF-2016R1A5A1010764 to J.W.C). Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/6/21

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N2 - For both fluorescence imaging and isolation of glycosidases in cells, we prepared novel activity-based, trifunctional fluorogenic probes that consist of (1) a sugar moiety as a glycosidase substrate, (2) a fluoromethylated coumarin for fluorescent labeling, and (3) an alkyne tag for click reaction to enable isolation of the labeled enzyme. One probe, β-GlcNAc-CM-F, was employed to fluorescently detect endogenous O-GlcNAcase in cells and to isolate the labeled enzyme by affinity chromatography.

AB - For both fluorescence imaging and isolation of glycosidases in cells, we prepared novel activity-based, trifunctional fluorogenic probes that consist of (1) a sugar moiety as a glycosidase substrate, (2) a fluoromethylated coumarin for fluorescent labeling, and (3) an alkyne tag for click reaction to enable isolation of the labeled enzyme. One probe, β-GlcNAc-CM-F, was employed to fluorescently detect endogenous O-GlcNAcase in cells and to isolate the labeled enzyme by affinity chromatography.

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Trifunctional Fluorogenic Probes for Fluorescence Imaging and Isolation of Glycosidases in Cells

Abstract

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